Indole-derived arynes and their Diels-Alder reactivity with furans.

  title={Indole-derived arynes and their Diels-Alder reactivity with furans.},
  author={Keith R. Buszek and Diheng Luo and Mikhail V. Kondrashov and Neil C. M. Brown and David VanderVelde},
  journal={Organic letters},
  volume={9 21},
Arynes derived from any position of the ubiquitous indole nucleus are unknown. We have now provided the first evidence for the formation and trapping of the 4,5-, 5,6-, and 6,7-indolynes. A series of o-dihalo indoles (Cl, Br, F) were synthesized and reacted under metal-halogen exchange conditions to give Diels-Alder cycloadducts in high yield with furan. The use of an excess of tert-butyllithium resulted in the rearrangement of the initially formed cycloadduct; however, employing only a slight… CONTINUE READING